Obituary of Matthew Andrews Jacobson

Matthew A. “Matt” Jacobson passed away peacefully after a period of illness on Monday, March 20, 2023. Matt was born in 1956 in Greenwich, Connecticut to Joan (Minot) of Westport, CT  and Henry Jacobson of New York, NY.. He attended Kent School in Kent, CT and then Amherst College in Amherst, MA, where he played basketball, majored in Russian Literature, and graduated with honors in 1977.

Matt quickly discovered a passion for horses and horse racing and was a successful trainer in the Northeast for many years before ultimately moving to central Kentucky with his family in the early 1990s. Shortly afterward he put his training on hold in order to spend more time with his family; he then worked for 10+ years building a strong career in financial services. In the 2000’s he returned to training and breeding in the thoroughbred industry, achieving innumerable wins, including most notably the 2010 Kentucky Cup Turf Stakes. He had a reputation for turning undervalued horses into winners with his sharp eye for ability and intuitive training strategies.  

In 1980, Matt met and married Elizabeth Osborn of Cleveland, OH. They were married for 35 years and raised four children: Leah, Joan Cary, Theodore (Teddy), and Frederich (Eric). Matt loved his children deeply and always spoke proudly about their lives and accomplishments.

People remember Matt as one of the funniest and most intelligent people they knew. He was unmissable in Versailles and Lexington as the loud, fast-talking guy from New England. Matt was a staunch conservative and devout Christian who was passionate and vocal in his beliefs and always willing to help someone in need. He loved sports, fishing, art, music, and animals. He had a special gift for handicapping and loved his time at the track surrounded by friends and horses. Matt had many dear friends and will be greatly missed.

Matt is predeceased by his son Teddy Jacobson, sister Abby Jacobson, and parents Henry Jacobson and Joan Minot. He leaves behind his three children: Eric, Leah, and Joan Cary, as well as grandchild Elliot, brother Paul, and sister Katy. 

A memorial service will be held on April 29, 2023 from 11 am - 1 pm at the Clark Legacy Center, 3000 Versailles Rd, Frankfort, KY.  In lieu of flowers, please send donations to Western Reserve Academy designated to the Teddy L. Jacobson memorial fund.